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60+ Weird Questions to Ask a Girl - Discovering Her Darkest Sides

calendarJune 12, 2017
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In a relationship, or when you are getting to know a girl, there are some mind bugling and crazy questions you may want to ask. Some of them, you want to ask because you really want to know; some because you want to get naughty, and others because you are just bored. Some of these questions can be very awkward, would make the girl feel uncomfortable, and put her on the spot.

If you want to find out some things about her, and you are looking for some awkward questions to ask a girl, this article will give you a list of awkward questions to ask her.

Awkward questions are the questions that cause people to feel uncomfortable. They may be related to sex, relationships or any other social topic.

You will find that some of these questions are crazy, sexually suggestive, very personal, inappropriate and weird. Most of these questions are not to be asked at the early stage of a relationship, but when you both have gotten to that extent of asking intimate questions.

On this list, you will also find some questions you should NEVER ask her. This article will not just impose ideas on you; it will also give you reasons why you should or should not ask your girl a particular question.


Inappropriate Questions to ask a Girl

1. What is the longest time you've stayed without having a shower?

This is a very crazy question to ask any girl. In serious conversations, a girl may not answer this question sincerely, because she wouldn’t want you to see her as a dirty girl. But when you are playing the Question and Answer game, it would be a fun question to ask.

2. Have you ever been arrested?

This is a very sensitive question, but it is necessary for you to ask. You definitely would want to know if you are dealing with an ex convict; so go ahead and ask about her criminal records and what crimes she has committed. If she feels uncomfortable answering this question, tell her something reassuring just to get her to trust you and open up.

awkward question to ask a girlSource

3. Have you ever taken drugs or been arrested for drugs?

Here goes another sensitive question which you need to ask nevertheless. You need to find a way to ask this questions before you start any form of relationship with a girl. Knowing the answer to this question could determine how far you may want to go with the relationship.

4. Why are you single at this moment?

This question may bring back unpleasant memories from her past, but it is necessary that you ask it anyway. You need to know exactly why she is single. It may interest you to know the reason for her last breakup. This information could help you know the kind of person she is. It could be your only chance of finding out if she’s a difficult person who no one wants to date. The mistakes of her ex could also make you know what could possibly make her walk away from you sometime in the future.

5. Have you ever stolen goods from a store?


This is one of the most uncomfortable questions you could ever ask anyone. This is not the kind of question you can just ask her out of the blues; you must have a cogent reason before asking this question. This question is necessary when you are trying to determine her views on morality, or the kind of things she’s capable of. You can also ask this question when you are bored; the ensuing answer might just be fun.

6. How much do you earn presently?

This is a very embarrassing question that you shouldn’t be asking. Asking a question like this suggests that you are only interested in her money, and that would be a very negative vibe to pass. You better wait until she’s ready to share that information with you.

7. Why did your last relationship end?

This question may put her in an awkward position, but it is very important that you ask anyway. Knowing the reason for her last breakup may help you plan your relationship better.

8. How many guys have you been involved with?

This question is going to make her uncomfortable. Are you sure you really want to know the answer?

9. How long should a couple be together before having sex?

This question is not just awkward; it may also make you look like a playboy who’s there only for the sex. However, you know you want to hear the answer to this question; so go ahead and ask.

10. Which would you choose between love and money?

Truth is, women always prefer men who are financially stable, but she may not admit that she will choose a rich man over you. However, ask this question and see what her response would be.

awkward questions to ask a girl

11. What is your most embarrassing moment in public?

Just brace up and get ready for an interesting answer.

12. Have you ever been involved with another girl?

This is a very awkward question you shouldn’t be asking her. Even if she shows lesbian tendencies, it is best to wait for her to bring up the topic.

13. Are you on your periods?

This question will make her feel awkward and very uncomfortable, so you better avoid it.

14. Am I the kind of guy that you are looking for?

This question might be awkward for her if she is just getting to know you. Please let her know more about you before you ask her a question like this.

15. What is your bust size?

A girl will find this question awkward. No ifs, no buts, no maybes! By all means possible, do not ask this question at the beginning of a relationship; save it for later.

16. Will we be sharing the bill?

If it is the first date, just be the man and pay the bill because no woman would be delighted to hear this.

17. What is the craziest thing that you have ever done in your entire life?

It is better not to share these things sometimes. If she wants to share them with you, then that is good for you. But the reality is that some things are better left undisclosed.

18. Have you ever done an HIV test?

Though this question would sound awkward to even you, it is very important that you ask. In fact, make sure you ask this question before getting sexually involved with her.

19. Have you ever had someone pee in your mouth?

This is an awkward and nasty question to ask her. If you are thinking about crazy questions, then this is one of them. Mind you, this isn't exactly a good question to ask your crush.

20. Have you ever felt stupid on a date?

This is one of the funny questions to ask a girl you like. Expect very funny answer, especially if the girl is the chatty type.

21. How long did your previous relationship last?

Awkward or not, the answer to this question will give you an idea of how long she’s willing to stay in a relationship.

Awkward Sexual Questions to Ask a Girl

1. Can I kiss you?

This might be hard for her to answer. It doesn’t matter if she says yes or no; if the mood is right, go ahead and ask this question.

awkward sexual questions to ask a girl

2. Does size matter to you?

This is very crazy question to ask a girl. Before you ask this, prepare your mind because her honest answer might trample your self-esteem.

3. What is your favorite sex position?

This is a hot question to ask a girl. Many females will find it awkward, but it would be a good way to get her to talk crazy.

4. Where is the most romantic place that you would like to have sex?

This is one of those intimate questions that you stir up her wild fantasies.

5. What time of the day do you most enjoy having sex?

This question, though a bit awkward, could help spice up your sexual relationship with her.

6. Have you ever taken money for sex?

This is one of those embarrassing questions that you shouldn’t ask your girlfriend, unless if you think that you’re dating a former prostitute. However, this question will not go down well with her.

7. Have you ever been sexually abused by a friend or relative?

When you ask this kind of question, you may be opening up some old wounds that she has been concealing over the years. Approach this question with caution.

8. Have you ever been physically abused by a previous partner?

Questions like these are super personal questions. Sometimes, it is very difficult for persons to share these experiences with you. If she does not want to talk about it then please understand.

9. What is the strangest location that you would like to have sex?

This is a hot question which could help spice up your sex life with her.

10. Would you ever have sex in the movie theater?

This is a crazy question that would give her erotic thoughts. If you want to stir up her sexual fantasies, ask her this question.

11. Would you ever have sex in a church?

This awkward question will get her thinking for a while.

12. Would you masturbate in my presence?

This is a very naughty question to ask you girl. As awkward as it may sound, it could lead to a crazy new adventure.

13. Have you ever had phone sex?

The idea of phone sex will sound adventurous to her, especially if she hasn’t done it before. You could get lucky and be the one to teach her. So go ahead and ask this awkward question.

14. When did you lose your virginity?

This is a personal question for many girls. This question can also cause a lot of embarrassment if the girl lost her virginity at an early age.

15. Have you ever used a sex toy?

This is an embarrassing question, but it all depends on how long you have been with her.

16. Is your ex-boyfriend’s penis bigger than mine?

Whilst this question would be embarrassing to the girl, you need to also brace up for the answer because you may not like the response you would get.

17. Have you ever faked it?

weird questions to ask a girl

I bet you can’t wait to hear the answer to this one. This is one of those questions that will have a funny answer; and may even hurt your ego and affect your sexual relationship. Are you sure you still want to ask this?

18. How long do you think we need to date before we get married?

It is very important to wait until the right time before you ask this question.

19. How long do we need to date before we have sex?

This can be a very awkward question for many girls. You can ask it at the beginning of the relationship to know exactly what you are getting into; but be careful because she may see it as a red flag.

20. Which role do you usually play in bed: The dominant or submissive role?

This question might be awkward for her, but if you have been in a relationship with her for a while, then you can ask her. Most women prefer to be the submissive, but who knows? Maybe that is not the case with her.

21. Do you like to talk naughty things with your partner?

Some females are shy and do not like to talk naughty with their partners. Ask her to know if she likes it, you never can tell; she may have been looking for a way to talk dirty, but did not want to appear vulgar.

super personal questionsSource

22. Have you ever done the 69 position with a guy?

This question could be both awkward and sexually suggestive. Asking this would help you know how far she has gone sexually, so you’ll step up your game when you get down with her.

23. Have you ever slept naked?

She shouldn’t have a problem answering this question. So go ahead and ask.

24. Do you prefer making love with the lights on or off?

This is another hot and intimate question to ask a girl. She wouldn’t have a problem answering. However, don’t ask this at the early stage of a relationship.

25. Do you like it rough or gentle?

This question is better reserved for a girl you are already in a relationship with. If you are on a date for the first time with a girl, then do not ask her this question.

26. Do you have any wild sexual fantasies?

Many girls will find it weird and awkward to disclose this information to you, especially if she is just getting to know you. Don’t ask questions like this till later in the relationship.

27. Where do you like to be kissed?

This is an awkward question for a girl to answer, but ask her anyway. And when you find the answer, make sure you always kiss her at that spot always.

28. At what age did you start to masturbate?

This is an extremely awkward question to ask any girl, and only a girl who totally trusts that you wouldn’t judge her will answer this sincerely.

29. Do you like watching porn?

Some persons like to watch porn, while others do not. If you like porn, it is best that you ask her this before you try watching porn around her.

30. Do you like giving or receiving oral sex?

This is another awkward question to ask, especially if she’s the shy type.

31. Have you ever had anal sex?

This is a super awkward question to ask her. Not every girl will be comfortable to answer this.

32. If you are given the chance, would you do a threesome?

Sometimes, you need to ask awkward questions like this so that you know the type of person she is. It will also make you know the kind of things she is capable of doing.

33. Which sexual position do you absolutely hate?

This is another awkward question from list. I bet you really want to know the answer to this question; so go ahead and ask her.

34. Have you ever had sex in water? Did you like it?

If she has done this before, and liked it; or she is willing to experiment with it, then there is more adventure waiting for the both of you.

35. Have you had sex in a car?

The answer to this question would show you just how naughty she can be.

inappropriate questions to ask a girlSource

36. Which size of penis do you prefer? Regular, or gigantic?

She will definitely find this embarrassing, but ask her nevertheless.

37. What are some of the sounds that you make during sex?

This is a weird question to ask a girl. She will feel so embarrassed to make those sounds for you.

38. Do you have a vibrator? How often do you use it?

This is a very awkward question to ask a girl. This may show you just how often she craves for sex.

39. Have you ever had sexual fantasies about a family member?

This is the most awkward, inappropriate and weird question to ask any girl. It is better not to ask a question like this one.

Read also:

There you have it; a list of 60 most awkward questions to ask your girlfriend. So in case you want to ask her some awkward questions, now you know the questions to ask, and what to expect. What is the most awkward question you've heard in your life? Share in comments!

Watch the women' answers to the questions that men are too afraid to ask in this video:

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